SYNTHESES OF (2S,3R)-METHYLGLUTAMIC AND (2S,3S)-3-METHYLGLUTAMIC ACID

被引：26

作者：

HARTZOULAKIS, B ^{[1
]}

GANI, D ^{[1
]}

机构：

[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 18期

关键词：

D O I：

10.1039/p19940002525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arndt-Eistert homologation of suitably-protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3- Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether. of cyclo-(R-Val-Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid. Both conjugate additions occurred with high diastereoselectivity.

引用

页码：2525 / 2531

页数：7

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